Tetrabutylammonium Fluoride → {9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methyl methanesulfonate

HRID 2268416Notes

Reaction equation

HRID 2268416 reaction equation
[CH3:1][S:2]([O:5][CH2:6][C:7]1[N:15]=[C:14]2[C:10]([N:11]=[CH:12][N:13]2[C@H:16]2[C@H:20]([O:21][Si](C(C)(C)C)(C)C)[C@H:19]([O:29][Si](C(C)(C)C)(C)C)[C@@H:18]([CH2:37][O:38][CH3:39])[O:17]2)=[C:9]([NH:40][CH2:41][CH:42]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[N:8]=1)(=[O:4])=[O:3].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:1][S:2]([O:5][CH2:6][C:7]1[N:15]=[C:14]2[C:10]([N:11]=[CH:12][N:13]2[C@H:16]2[C@H:20]([OH:21])[C@H:19]([OH:29])[C@@H:18]([CH2:37][O:38][CH3:39])[O:17]2)=[C:9]([NH:40][CH2:41][CH:42]([C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)[C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[N:8]=1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86757641{9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methyl methanesulfonate

Product 1

HCID 59975278{9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methyl methanesulfonateYield 81.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

{9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methyl methanesulfonate (240 mg, 0.3 mmol) (preparation 16) was dissolved in stirred tetrahydrofuran (1 ml) and a 1 molar solution of tetra-n-butylammonium fluoride in tetrahydrofuran (0.6 ml, 0.6 mmol) added. The reaction mixture was stirred at room temperature for 24 hr. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol (95:5) increasing in polarity to dichloromethane:methanol (90:10). This gave the title compound (140 mg) as a foam. MS: 570 (MH+).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol (95:5)
  3. temperatureincreasing in polarity to dichloromethane:methanol (90:10)

Sources & evidence

ORD record
ord-496b9eeebb204754b45ef806d2457bbb
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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